Cobalt−NHC Catalyzed C(sp2)−C(sp3) and C(sp2)−C(sp2) Kumada Cross-Coupling of Aryl Tosylates with Alkyl and Aryl Grignard Reagents

Aleksandra Piontek, Wioletta Ochędzan-Siodłak, Elwira Bisz, Michal Szostak

Research output: Contribution to journalArticlepeer-review

Abstract

The first cobalt-catalyzed cross-coupling of aryl tosylates with alkyl and aryl Grignard reagents is reported. The catalytic system uses CoF3 and NHCs (NHC=N-heterocyclic carbene) as ancillary ligands. The reaction proceeds via highly selective C−O bond functionalization, leading to the corresponding products in up to 98 % yield. The employment of alkyl Grignard reagents allows to achieve a rare C(sp2)−C(sp3) cross-coupling of C−O electrophiles, circumventing isomerization and β-hydride elimination problems. The use of aryl Grignards leads to the formation of biaryls. The C−O cross-coupling sets the stage for a sequential cross-coupling by exploiting the orthogonal selectivity of the catalytic system.

Original languageEnglish (US)
JournalChemCatChem
DOIs
StateAccepted/In press - 2020

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Keywords

  • C(sp)−C(sp) cross-coupling
  • cobalt catalysis
  • cross-coupling
  • C−O activation
  • sustainability

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